IE34076L - Imidazolidinones. - Google Patents
Imidazolidinones.Info
- Publication number
- IE34076L IE34076L IE700380A IE38070A IE34076L IE 34076 L IE34076 L IE 34076L IE 700380 A IE700380 A IE 700380A IE 38070 A IE38070 A IE 38070A IE 34076 L IE34076 L IE 34076L
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- methyl
- reacting
- formula
- dibenz
- Prior art date
Links
- 150000008624 imidazolidinones Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- 229910052783 alkali metal Inorganic materials 0.000 abstract 4
- 150000001340 alkali metals Chemical class 0.000 abstract 4
- 150000002148 esters Chemical class 0.000 abstract 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 230000000911 decarboxylating effect Effects 0.000 abstract 3
- 230000003301 hydrolyzing effect Effects 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 229940044613 1-propanol Drugs 0.000 abstract 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 abstract 2
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 abstract 2
- DKGQENSYEBYPNT-UHFFFAOYSA-N 1-(3-chloro-2-methylpropyl)-4-methylpiperazine Chemical compound ClCC(C)CN1CCN(C)CC1 DKGQENSYEBYPNT-UHFFFAOYSA-N 0.000 abstract 1
- BKWPKBBPNYTXEP-UHFFFAOYSA-N 1-(3-chloropropyl)-3-ethylimidazolidin-2-one Chemical compound CCN1CCN(CCCCl)C1=O BKWPKBBPNYTXEP-UHFFFAOYSA-N 0.000 abstract 1
- RQAVSDINDRNIKL-UHFFFAOYSA-N 1-chloro-3-isocyanatopropane Chemical compound ClCCCN=C=O RQAVSDINDRNIKL-UHFFFAOYSA-N 0.000 abstract 1
- SNTKNKWMWUQCAQ-UHFFFAOYSA-N 11-(2-methyl-3-piperazin-1-ylpropyl)-5,6-dihydrobenzo[b][1]benzazepine Chemical compound CC(CN1C2=C(CCC3=C1C=CC=C3)C=CC=C2)CN2CCNCC2 SNTKNKWMWUQCAQ-UHFFFAOYSA-N 0.000 abstract 1
- MRYZYDROBYBPJA-UHFFFAOYSA-N 11-(2-methyl-3-piperazin-1-ylpropyl)benzo[b][1]benzazepine Chemical compound CC(CN1C2=C(C=CC3=C1C=CC=C3)C=CC=C2)CN2CCNCC2 MRYZYDROBYBPJA-UHFFFAOYSA-N 0.000 abstract 1
- XAOPUYQJGNFAMR-UHFFFAOYSA-N 11-(3-chloro-2-methylpropyl)benzo[b][1]benzazepine Chemical compound ClCC(CN1C2=C(C=CC3=C1C=CC=C3)C=CC=C2)C XAOPUYQJGNFAMR-UHFFFAOYSA-N 0.000 abstract 1
- AOVCTDSUDHZIHL-UHFFFAOYSA-N 11-[2-methyl-3-(4-methylpiperazin-1-yl)propyl]-5,6-dihydrobenzo[b][1]benzazepine Chemical compound CC(CN1C2=C(CCC3=C1C=CC=C3)C=CC=C2)CN2CCN(CC2)C AOVCTDSUDHZIHL-UHFFFAOYSA-N 0.000 abstract 1
- BELGHMWMXFCZTP-UHFFFAOYSA-N 3-ethyl-1,3-oxazolidin-2-one Chemical compound CCN1CCOC1=O BELGHMWMXFCZTP-UHFFFAOYSA-N 0.000 abstract 1
- CLQOSHIIXSAWAY-UHFFFAOYSA-N 4-[3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-2-methylpropyl]piperazine-1-carbonitrile Chemical compound C1=CC=CC=2N(C3=C(CCC21)C=CC=C3)CC(CN3CCN(CC3)C#N)C CLQOSHIIXSAWAY-UHFFFAOYSA-N 0.000 abstract 1
- LCGTWRLJTMHIQZ-UHFFFAOYSA-N 5H-dibenzo[b,f]azepine Chemical class C1=CC2=CC=CC=C2NC2=CC=CC=C21 LCGTWRLJTMHIQZ-UHFFFAOYSA-N 0.000 abstract 1
- ZSMRRZONCYIFNB-UHFFFAOYSA-N 6,11-dihydro-5h-benzo[b][1]benzazepine Chemical compound C1CC2=CC=CC=C2NC2=CC=CC=C12 ZSMRRZONCYIFNB-UHFFFAOYSA-N 0.000 abstract 1
- KYJVCHIXVPWNLY-UHFFFAOYSA-N [2-methyl-3-(4-methylpiperazin-1-yl)propyl] acetate Chemical compound CC(CN1CCN(CC1)C)COC(C)=O KYJVCHIXVPWNLY-UHFFFAOYSA-N 0.000 abstract 1
- CLEANLBCNTZFQQ-UHFFFAOYSA-N [3-(4-cyanopiperazin-1-yl)-2-methylpropyl] acetate Chemical compound CC(CN1CCN(CC1)C#N)COC(C)=O CLEANLBCNTZFQQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- AYPMQEANBWYSEV-UHFFFAOYSA-N ethyl 4-(3-benzo[b][1]benzazepin-11-yl-2-methylpropyl)piperazine-1-carboxylate Chemical compound C(C)OC(=O)N1CCN(CC1)CC(CN1C2=C(C=CC3=C1C=CC=C3)C=CC=C2)C AYPMQEANBWYSEV-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Laminated Bodies (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1,261,007. Dibenzazepine derivatives. J. R. GEIGY A.G. 26 March, 1970 [28 March, 1969; 21 May, 1969], No. 14637/70. Heading C2C. Novel compounds of Formula I (in which X is H or Cl, m is 2 or 3, R 1 is methyl or ethyl, each of R 2 and R 3 is H or R 2 and R 3 together represent an additional bond) and their acid addition salts, are prepared by (a) reacting a reactive ester of a compound of Formula II with a compound of Formula III or an alkali metal derivative thereof, or (b) reacting a compound of Formula IV or an alkali metal derivative thereof, with a reactive ester of a compound of Formula V or (c) reacting a reactive ester of a compound of Formula VI with a compound of Formula VII in the presence of a basic condensation agent, or (d) reacting a compound of Formula III or an alkali metal derivative thereof, with a compound of Formula VIII (in which Y is halogen) or an alkali metal derivative thereof, and, if desired, converting a resulting free base into an acid addition salt thereof. 5 - [2 - Methyl - 3 - (1 - piperazinyl) - propyl]- 10,11-dihydro-5H-dibenz[b,f]azepine is prepared by reacting 10,11-dihydro-5H-dibenz[b,f]azepine with 1-(3-chloro-2-methyl-propyl)-4-methyl piperazine to form 5-[2-methyl-3-(4-methyl-1- piperazinyl) - propyl] - 10,11 - dihydro - 5H- dibenz[b,f]-azepine, reacting this compound with cyanogen bromide to form 4-[3-(10,11-dihydro- 5H - dibenz[b,f]azepin-5-yl) - 2 - methyl - propyl]- piperazine-1-carbonitrile and simultaneously hydrolysing and decarboxylating this compound by treatment with hydrochloric acid. The corresponding 3-chloro compound is prepared analogously. 5 - [2 - Methyl - 3 - (1 - piperazinyl) - propyl]- 5H-dibenz[b,f]azepine is prepared by reacting 5- (3 - chloro - 2 - methyl - propyl) - 5H - dibenz- [b,f]azepine with 1-piperazine carboxylic acid ethyl ester to give 4-[3-(5H-dibenz[b,f]azepine-5- yl)-2-methyl-propyl]-piperazine-1-carboxylic acid ethyl ester and simultaneously hydrolysing and decarboxylating this compound by treatment with potassium hydroxide. Compounds of Formula VI and their esters are prepared by reacting #,4-dimethyl-piperazine-1- propanol with acetic anhydride to give 1-(2- methyl-3-acetoxypropyl)-4-methylpiperazine, reacting this compound with cyanogen bromide to form 4-(2-methyl-3-acetoxypropyl)-1-piperazine carbonitrile, hydrolysing arid simultaneously decarboxylating this compound by treatment with hydrochloric acid to give #-methyl-piperazine-1- propanol, reacting this compound with a 1- (haloalkyl)-3-R 1 -2-imidazolidinone and esterifying the resulting compound VI, e.g. by treatment with thionyl chloride or tosyl chloride. 1-(3-Chloropropyl)-3-ethyl-2-imidazolidinone is prepared by reacting 3-ethyl-2-oxazolidinone with (3-chloropropyl)-isocyanate. Compounds of Formula VIII are prepared by reacting diethanolamine with a 1-R 1 -isocyanate to form a 1-R 1 -3,3-bis-(2-hydroxyethyl)-urea and halogenating this compound, e.g. by treatment with thionyl chloride. Pharmaceutical compositions for oral, rectal or parenteral administration comprise a compound of Formula I or a pharmaceutically acceptable acid addition salt thereof, together with a pharmaceutical carrier. The compositions are useful in the treatment of psychosomatic disturbances.
[GB1261007A]
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH479969A CH505122A (en) | 1969-03-28 | 1969-03-28 | Imidazolidinone derivs; psychosomatic agents - and antiemetics |
| CH769369 | 1969-05-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE34076L true IE34076L (en) | 1970-09-28 |
| IE34076B1 IE34076B1 (en) | 1975-01-22 |
Family
ID=25696308
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE380/70A IE34076B1 (en) | 1969-03-28 | 1970-03-26 | Process for the production of new imidazolidinone derivatives |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US3646037A (en) |
| JP (1) | JPS4928519B1 (en) |
| AT (1) | AT294074B (en) |
| BE (1) | BE748098A (en) |
| BG (4) | BG18185A1 (en) |
| DE (1) | DE2014911A1 (en) |
| DK (1) | DK127116B (en) |
| FR (1) | FR2035971B1 (en) |
| GB (1) | GB1261007A (en) |
| IE (1) | IE34076B1 (en) |
| IL (1) | IL34173A (en) |
| NL (1) | NL7004059A (en) |
| NO (1) | NO127151B (en) |
| PL (1) | PL72352B1 (en) |
| SE (1) | SE379044B (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE754641A (en) * | 1969-08-11 | 1971-02-10 | Geigy Ag J R | IMIDAZOLIDINONE DERIVATIVES AND MEDICINAL PRODUCTS CONTAINING SUCH DERIVATIVES |
| BE754640A (en) * | 1969-08-11 | 1971-02-10 | Geigy Ag J R | IMIDAZOLIDINONE DERIVATIVES AND MEDICINAL PRODUCTS CONTAINING SUCH DERIVATIVES |
| BE754642A (en) * | 1969-08-11 | 1971-02-10 | Geigy Ag J R | IMIDAZOLIDINONE DERIVATIVES AND MEDICINAL PRODUCTS CONTAINING SUCH DERIVATIVES |
| GB1323659A (en) * | 1971-04-10 | 1973-07-18 | Yoshitomi Pharmaceutical | Piperazine derivatives methods for their production and pharmaceuticl compositions containing them |
| US4006144A (en) * | 1972-07-21 | 1977-02-01 | Hoffmann-La Roche Inc. | 10,11-Dihydro-dibenzo(b,f)thiepin derivatives |
| US4006145A (en) * | 1972-07-21 | 1977-02-01 | Hoffmann-La Roche Inc. | 10,11-Dihydro dibenzo(b,f)thiepin derivatives |
| US4044010A (en) * | 1973-03-30 | 1977-08-23 | Hoffmann-La Roche Inc. | Dibenzo[b,f] thiepins bearing piperazinyl substitution |
| AU741839B2 (en) | 1996-10-04 | 2001-12-13 | Novo Nordisk A/S | N-substituted azaheterocyclic compounds |
| CA3042927C (en) | 2009-05-05 | 2022-05-17 | Arbutus Biopharma Corporation | Lipid compositions for the delivery of therapeutic agents |
-
1970
- 1970-03-20 DK DK142070AA patent/DK127116B/en unknown
- 1970-03-20 NL NL7004059A patent/NL7004059A/xx unknown
- 1970-03-20 SE SE7003836A patent/SE379044B/xx unknown
- 1970-03-20 NO NO01060/70A patent/NO127151B/no unknown
- 1970-03-26 GB GB04637/70A patent/GB1261007A/en not_active Expired
- 1970-03-26 DE DE19702014911 patent/DE2014911A1/en active Pending
- 1970-03-26 IE IE380/70A patent/IE34076B1/en unknown
- 1970-03-26 JP JP45025205A patent/JPS4928519B1/ja active Pending
- 1970-03-26 IL IL34173A patent/IL34173A/en unknown
- 1970-03-26 US US24392A patent/US3646037A/en not_active Expired - Lifetime
- 1970-03-27 BE BE748098D patent/BE748098A/en unknown
- 1970-03-27 BG BG17250A patent/BG18185A1/xx unknown
- 1970-03-27 FR FR707011168A patent/FR2035971B1/fr not_active Expired
- 1970-03-27 AT AT286970A patent/AT294074B/en active
- 1970-03-27 BG BG014298A patent/BG17315A3/en unknown
- 1970-03-27 PL PL1970139664A patent/PL72352B1/xx unknown
- 1970-03-27 BG BG017249A patent/BG17792A3/en unknown
- 1970-03-27 BG BG017248A patent/BG17579A3/en unknown
-
1971
- 1971-09-20 US US00182214A patent/US3767796A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE2014911A1 (en) | 1970-10-22 |
| NO127151B (en) | 1973-05-14 |
| BG18185A1 (en) | 1974-09-02 |
| BG17579A3 (en) | 1973-11-10 |
| IE34076B1 (en) | 1975-01-22 |
| FR2035971A1 (en) | 1970-12-24 |
| SE379044B (en) | 1975-09-22 |
| BE748098A (en) | 1970-09-28 |
| PL72352B1 (en) | 1974-06-29 |
| GB1261007A (en) | 1972-01-19 |
| US3646037A (en) | 1972-02-29 |
| BG17315A3 (en) | 1973-07-25 |
| JPS4928519B1 (en) | 1974-07-26 |
| BG17792A3 (en) | 1973-12-25 |
| NL7004059A (en) | 1970-09-30 |
| IL34173A0 (en) | 1970-05-21 |
| DK127116B (en) | 1973-09-24 |
| IL34173A (en) | 1972-12-29 |
| US3767796A (en) | 1973-10-23 |
| FR2035971B1 (en) | 1973-04-06 |
| AT294074B (en) | 1971-11-10 |
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